


Lester's gang

by jay_jay_1029



Category: Phandom/The Fantastic Foursome (YouTube RPF)
Genre: M/M
Language: English
Status: In-Progress
Published: 2016-02-18
Updated: 2016-04-20
Packaged: 2018-05-21 10:54:35
Rating: Not Rated
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 3
Words: 7,026
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6048817
Author URL: https://archiveofourown.org/users/jay_jay_1029/pseuds/jay_jay_1029
Summary: <blockquote class="userstuff">
              <p>Crappy title, I know. Basically Phil runs a gang and Dan borrowed money from the gang that he couldn't pay off, so he had to pay it off through "other" means(i.e. sexual things). I wrote this at nine in the morning after not sleeping that night so I was very sleep deprived, sorry if it's got problems.<br/>*WARNINGS* Dub-con, gangs, guns, cursing, sex, blowjobs, threatening, danger, blowjobs, abuse; Do not read if any of these things make you uncomfortable.<br/>Side note: I want to say that I do not condone what Phil does to Dan. This is not a story about a perfect love, it's a story about something extremely messed-up and dangerous and bad.</p>
            </blockquote>





	1. Part 1

**Author's Note:**

> I would like to say again, I do not condone nor agree with what Phil does in this chapter. While Dan does technically consent, it is only because he doesn't believe he has any other options. Therefore, it does fall into the category of rape, and is therefore not okay.

How the hell did Dan get himself into this mess?

He knew exactly how, but he still found himself asking this question as he walked to the door of the apartment building where his meeting was scheduled. His meeting with Mr. Lester, the head of the gang he had gotten himself mixed up with.

If only he hadn't needed money three months ago. If only he hadn't needed money for his apartment. Now, of course, he was able to pay for his apartment on his own. The problem, though, was that he didn't have enough to pay the gang back yet.

He was saving up for it, of course. He was just a few hundred short. But the deal had, in fact, been that he would pay it off in full, exactly two months later. He had already gotten an extension on it once.

When he had tried to get a second one, they told him he had a meeting with their leader.

And that's how Dan ended up like this, in front of the door to the apartment with his heart racing, and trying to get the courage to knock. He tried not to think too hard about the fact that if he didn't do this perfectly, he could end up dead.

Dan took a deep breath, banished the thought from his mind, and knocked on the door. It opened to reveal a man holding a gun at him, causing him to tense up, his eyes widening. "Code word in ten seconds or I shoot."

"S-Snap!" He stuttered quickly, praying to any god out there that he got the code word right. Thankfully, one of them seemed to be listening, as the man in front of him lowered the gun and stepped aside, gesturing to the stairs leading down. Dan gulped and nodded, walking that way shakily. He tried to ignore the smirk on the face of the man with the gun.

Dan began walking down the steps, holding on tightly to the banister so he didn't fall down. He got to the door at the bottom of the stairs, taking another deep breath before knocking on the door, three times slow and three times fast. There was a pause before the door opened, another man with a gun standing there.

"You're Howell, right?" He asked with a gruff, American voice. Dan nodded weakly, biting his lip. The man glared at him, grabbing Dan's chin roughly, causing Dan to let out a squeak of fear. "I asked you a fucking question, brat. Answer me or I'll shove this up your ass and pull the fucking trigger." The gun was pressed against his stomach.

"Y-yes!" Dan forced out. "I-I mean, yes sir! I-I-I'm h-here to s-see M-M-Mr. L-Lester!" Dan was shaking like a leaf, tears in his eyes as he believed he was going to die.

"Anderson, let him go," A voice from inside the room sounded. "It's fun to play, but if he's dead, we don't get our money." The man with the gun, apparently named Anderson(first or last name, Dan couldn't even tell), growled and let Dan go, stepping to the side to let Dan in. Dan weakly walked forwards, still shaking. "Leave, Anderson. I want to speak with Howell alone."

Anderson glared at Dan. "Try anything funny, and I'll make you eat your own intestines." Dan flinched away, still looking scared, as Anderson left the room and closed the door. Dan looked to where the voice had come from a moment ago, his breath catching at what he saw.

A man with dark black hair, dressed impeccably in a grey suit, was sitting on the other side of the posh room, in a large couch built into the corner of the wall. "Howell. Come and sit," He ordered, a smirk on his face. Dan hastily walked over, biting his lip and sitting next to the man. The raven-haired man held out his hand to Dan, and Dan shakily took it. "It's nice to finally meet you. I'm Phil Lester."

"I-I-I'm D-Dan. Dan Howell, s-sir," Dan stuttered, shaking his hand before pulling his hand away. "I-I came to t-talk about e-extending my d-due date for th-the loan." He hated how much his voice shook. Though it may have been because he could clearly see the outline of a gun in the man's left inner jacket pocket.

"Hm. I see. So you don't have the money yet, even though we've already given you an extra month?" Mr. Lester asked, raising an eyebrow. Dan shook his head, looking a bit guilty. "And why not?"

"M-my job ended up paying less than I anticipated, sir," He responded, trying to stay calm. "I-I almost have enough, though, sir. I-I swear, I'll get the money to you. I-it just may take a bit longer than I originally thought."

"Howell, do you know how many times I hear that every day?" Mr. Lester asked, his eyes showing anger but his voice calm. Dan shook his head, looking scared. "Almost a hundred times a day. And how many of the people saying that make it out alive?" Dan tensed up, looking terrified. "The answer is none, other than the ones who seem to miraculously find the money to pay me back," Mr. Lester answered before Dan could.

"S-sir, I-" Mr. Lester held up a hand.

"You, however, seem a bit different from them," He continued, not allowing Dan to speak. "Most of them come in here thinking they own the world. And most of them aren't nearly as good looking as you." Dan's eyes widened as he realized where this was probably going, but he stayed silent as Mr. Lester ran a thumb over his lower lip, their eyes locking. "And I don't think anyone with such a pretty mouth has come in here before. And it would be such a shame for me to ruin it by knocking your teeth out, don't you think?" Dan nodded quickly in agreement, not wanting to lose his teeth.

"S-so you'll g-g-give me th-the extension?" Dan asked hopefully. Mr. Lester chuckled darkly, shaking his head slightly. Dan felt a hand toying with his belt, and his eyes widened.

"Daniel, you have three options," Mr. Lester started, leaning in to whisper into Dan's ear while he got the belt undone. "Option one, you get me the money by the deadline that was agreed on." Dan felt a hand rubbing at his crotch, and he barely held in a moan. "Option two, you put that pretty mouth of yours to use, and I give you the extension." Mr. Lester tugged Dan into his lap, and Dan immediately felt how hard he was. "Or option three, you become my good little bitch, and you don't have to worry at all about the debt."

"And what if I don't want any of that?" Dan immediately felt something cold and hard pressed against his crotch through the material of his trousers, his eyes widening.

"Then I pull this trigger, and you lose your genitals," Mr. Lester growled into his ear. "And before you even say it, you /do/ have the option to get out of this. Just get me the money by the end of the day, and you won't have to lose your genitals, or put your mouth on mine. So your choice. Money, blowjob, or bitch."

Dan bit his lip and looked away. "A-and how long do I have to decide?" He asked timidly.

"About five seconds." Mr. Lester pressed the gun closer, causing Dan to whimper softly and squeeze his eyes shut tightly.

"P-please, please, don't..." He whimpered, shaking a bit as tears formed in his eyes. He felt Mr. Lester relax his grip a bit.

"Choose. Now," He growled into Dan's ear. "You can choose to give the money by the end of the day, and if you don't have it, then I'll shoot your poor little dick off. Or you can choose one of the other two options now."

Dan fidgeted on his lap, his breathing quickening as tears started dripping down his cheeks. "C-c-can I p-please h-have a f-f-few m-minutes t-to decide?" He opened his reddening eyes, pleading with them.

Mr. Lester thought for a moment before nodding, releasing his grip on Dan and pulling the gun away. "As long as you don't leave the room."

Dan quickly stood up and took a few steps back, trying to calm down. He took a few deep breaths, his back to Mr. Lester as he weighed his options.

He knew he couldn't get the money by the end of the day, so that option was out of the question. He wiped his eyes and sniffled to clear his nose.

Honestly, the idea of not having to worry about the debt sounded amazing. He could keep saving up at the pace he set, and pay it off when he could, and after that, simply cut it off after his debt was paid. But he didn't know if it was worth it. Choosing that option would be getting himself even deeper into this mess.

His other option was to just do it once, get it over with, and get an extra month to make the money. If he tried hard enough, he was sure he could do it, as long as he didn't slack off. He would have to seriously consider doing sponsored videos to be safe about it(if that was possible anymore) but he could certainly do it.

But he would lose so much sleep over it. He would be working himself to the bone for it. He would be putting himself through hell, when his other option was basically having sex and then never having to bother with it.

Those were his only two options. Unless...

"What if I g-gave you a blowjob now, a-and if I hate it, I-I'll just take the extension, b-but if I don't hate it, I-I l-let you d-do more, l-like you said before?" Dan bartered, turning around to face Mr. Lester, seeing him smirk at the suggestion.

"So you give me a blowjob, and if you don't hate it, you become my bitch. Otherwise, I get my money at the end of the month." Mr. Lester stood up and buttoned his suit jacket, stepping closer to Dan with an almost evil smirk. "You have a deal." He held his hand out for Dan to shake in agreement, and as Dan shook it, he couldn't help but feel he was making a deal with the devil.

He was proven right fairly quickly as Mr. Lester pulled him closer before shoving him to his knees, making him eye-level with Mr. Lester's crotch. "I suggest you get to work before I get impatient."

Dan took a deep breath and nodded, undoing Mr. Lester's belt before unzipping and unbuttoning his suit trousers, pulling them down a bit along with his boxers, gasping softly at the size. It was bigger than he had expected, and he couldn't help but imagine it ending up other places. He blushed and pushed the thoughts from his mind, taking a deep breath and pulling Mr. Lester's length into his mouth, as much as he could without gagging.

Dan looked up through his eyelashes at Mr. Lester, seeing him smirking. He gasped as his head was shoved further down onto the length in his mouth, gagging a bit around it. And then it really began. Mr. Lester began sliding in and out quickly, going deeper each time, fucking Dan's mouth almost violently, moaning at the gagging sounds Dan made.

Dan let his eyes slide shut, realizing he was enjoying the feeling, enjoying the fact that it made him gag. He slid his hand down, taking out his own length and starting to stroke it slowly, moaning softly in between gags. He gasped when he felt a foot push his hand away and then press into his crotch.

"I don't recall giving you permission to do that," Mr. Lester growled, shoving the tip of his shoe against Dan's cock, causing him to whimper, rocking into it a bit. "That's it." He yanked Dan away by the hair, his lips red and swollen now as he looked up at Mr. Lester, seeming surprised that he wasn't sucking anymore. Mr. Lester grabbed him by the hair and dragged him over to the couch, quickly striding over to his desk and taking out a pair of handcuffs, which he then put on Dan's wrists behind his back.

Dan tugged at them, eyes widening. "I-I didn't agree to this!" He said, his voice high with worry. All he got in reply was a smirk and a light slap to the face.

"And I didn't agree to getting my money so late. Now we're even." Before Dan could respond, Mr. Lester shoved his cock back into Dan's mouth, fucking into it fast and hard all over again while Dan moaned and gagged around it, his eyes sliding shut again as he found himself enjoying it.

Mr. Lester continued slamming into Dan's mouth, moaning loudly. His movements were quickly becoming erratic, until suddenly he was coming down Dan's throat. Dan gagged as he was forced to swallow it, as the liquid had no where else to go. Mr. Lester slowly pulled out, quickly pulling his pants up and redoing his belt, before taking out the gun and pointing it right at Dan's temple, causing him to whimper, looking scared.

"Now. Are you gonna pay me off by the end of the month, or are you gonna be my bitch?" Mr. Lester asked him, raising an eyebrow. Dan bit his lip, glancing down at his still exposed and fully erect cock, before he looked back at Mr. Lester.

"I-I w-wanna b-be- b-b-be y-your bitch. I-I w-want it, s-sir..." He could feel his heart racing. But he was sure about this. In that moment, all he could think about was taking this further.

Mr. Lester smirked at him, sitting on the couch next to him and pulling him into his lap. "Well, then," He started, reaching down to grip Dan around the base. "It seems we have a bit of work to do. Don't we, love?"

Dan could tell that this was going to be amazing.


	2. Part 2 - Fire

**Summary for the Chapter:**

> This time, Dan IS on fire.

**Notes for the Chapter:**

> As always, I do NOT condone what is happening in these stories. Do not read if you are triggered by extreme descriptions of pain/burning sensations.

Dan was regretting every descision he had ever made.  
It felt as if every inch of his skin was burning, it felt like it would melt off any second. He absently noticed the tears dampening the cloth around his eyes, but he barely focused on it as he focused more on the ache in all of his muscles from being in this position for so long.  
His hands were tied above his head, the chain being attached to the ceiling, with his feet barely brushing the ground so that he was nearly dangling rather than standing. He had a spreader bar attached to his ankles, and another at his knees, making it impossible to close his legs.  
Dan felt the man standing behind him rub more of the burning cream into his skin with gloves hands, causing him to cry out around the gag once more. He whimpered pathetically as the hands trailed lower, finishing the job and making sure every inch of exposed skin was lathered with the substance, including his limp member, dangling pathetically between his legs, showcasing just how little he was enjoying this.  
He thought that would be the most of the pain, but then he felt the gloved hands cup his arse cheeks, despite the fact that he already had cream there. And then he felt a lathered finger moving closer and closer to his hole, and he immediately began struggling as he realized what was about to happen. The man slapped his side harshly to make him stop before returning to what he was doing.  
Dan bit down hard on the cloth gag, his eyes squeezed shut behind the blindfold. He screamed into the cloth as the cream entered him, the burning sensation becoming so much more intense there on such a sensitive part of him. He felt tears dripping faster from his eyes, his breath heaving as he felt as though his insides were on fire.  
This whole situation reeked of irony, what with his screen name and all.  
Dan felt the fingers sliding in and out of him quickly, using the cream as lubricant to stretch him out, sobs escaping his mouth with each thrust in.  
This continued until Dan's hole was stretched enough to accomodate four fingers easily with hardly any resistance. He heard footsteps, a door opening and closing, and then quiet. The room was silent aside from Dan's whimpering and crying. He faded in and out of consciousness as exhaustion overtook him, and then pain woke him up crying again.  
Dan didn't know how long he was in there, but it felt like an eternity until he heard the door open and close again. He heard footsteps and felt a hand gently run through his hair, causing him to cry out softly against the gag and try to flinch away, struggling against the restraints again.  
"Now is that a way to greet the person who's gonna help you out of this?" A sultry voice Dan recognized said, causing him to stop struggling, eagerly leaning into the touch once he realized it was Phil, and not the person who put the cream on. "There we go. Such a good toy..." He murmured, gently petting Dan's hair. Dan sniffled and leaned into the touch, whimpering against the gag. He felt the spreader bars being fiddled with before they both came off, and he immediately closed his legs as much as possible.  
"There we go, love. I'll get you all cleaned up, I'll get rid of the burning for you. I'm guessing you didn't like the capsaicin cream that much, huh?" Phil soothed, running a cool, wet washcloth over Dan's burning skin. Dan shook his head to indicate that no, he didn't like it at all. "It's okay, love. Your punishment will be over soon. And I'm sure you know to never disrespect me again. Isn't that right?"  
Dan nodded quickly, making a large mental note to always be respectful. He never wanted to experience such pain again. "Good, good," Phil cooed, gently stroking Dan's cheek to calm him. Dan leaned into the comforting touch, trying to take deep breaths to stay calm. "My little toy is always gonna be good for its owner, isn't it?" Dan nodded again. He would be good, he would be a perfect angel if it meant never being punished again. "Good. Such a good little toy for your owner."  
Things continued like this for a while, with Phil cleaning the cream from Dan's skin yet ignoring his stretched-out, burning hole, all while whispering gentle words of comfort and encouragement to keep him calm. Eventually, when Phil was finally cleaning all of Dan's body with a washcloth aside from his hole, he undid the cuffs around his hands. Dan whimpered into the gag as his knees gave way and he nearly fell, but Phil caught him, holding him close. Dan felt himself being picked up and carried somewhere, being layed onto a comfortable bed he recognized quickly.  
Dan's vision flooded with light as the blindfold was removed, and he saw he was in Phil's room, laying in the bed they so often shared. Phil gently removed the gag that was soaked with spit and had many bite marks, gently putting both pieces of cloth on the bedside table. Dan stayed silent, not wanting to speak unless spoken to, as he didn't want more punishment.  
Phil picked up a tissue from the box on the bedside table, gently wiping Dan's eyes, nose, and mouth of tears, snot, and saliva respectively. Phil gently cleaned Dan's face off before gently cupping his cheeks. Dan leaned into the touch, his eyes drooping. The whole ordeal had tired him out immensely.  
"How are you feeling, baby?" Phil asked softly. Dan fidgeted a bit, biting his lip. Should he mention it? Or would that get him into trouble. "I asked you a question..." Phil reminded threateningly when Dan took long to respond.  
"Y-you forgot to c-clean the b-burning cream f-from ins-side," Dan blurted, his voice shaky. He heard Phil chuckle in response, shaking his head. Dan whimpered softly, biting his quivering lip. He wanted it out, he hated the burning feeling. It was almost worse this way, because all the pain was centered on one spot that he could focus on.  
"I didn't forget anything, toy," Phil corrected. "It's supposed to be there still. I left it there because your punishment isn't over. Did you think you were just stretched with it for the sake of fun? Because that isn't it at all." Dan let out another whine, realizing what was most likely about to happen. He hated this punishment. He wanted it to be over.  
"Now, unless you want your punishment to be much worse, get on your hands and knees in the middle of the bed," Phil ordered, and Dan scrambled to get into the right position. Phil knelt behind Dan on the bed, grabbing his legs and spreading them further apart. He stepped away and picked something up. Dan could hear the movement.  
Dan couldn't hold back a small cry of pain as he felt something pushing inside of him. He quickly realized that something was a large dildo, and it was covered in the same cream as before. "You need lube of some form, right? This is what you're getting," Phil told him, slowly working the long, thick, slightly phallic object into Dan, until the flared base was pressed against his hole and all but the base was inside of him. Dan whimpered in pain as he felt the large object stretching him uncomfortable, along with the burning cream making it so much worse.  
Dam thought that would be the last of it, but then he heard Phil moving some things around behind him. "S-sir? M-may I- uh, i-it, turn around and look at what you're doing?" He asked timidly, almost referring to himself as something other than it, which he knew wouldn't help right then. He didn't want this to get any worse than it already was.  
"No, it may not," Phil responded, making Dan whimper but stop talking, as he knew not to argye, lest he be punished more. That was what got him into this in the first place. Phil had told him that he was to only be referred to as it, and other objectifying terms, as it would supposedly help him learn his place as something Phil owned, until he could buy himself back by paying off the money he owed. Dan had argued with Phil about it, and then ended up getting this severe punishment that he absolutely hated.  
Dan felt Phil grab his hips and drag him along the bed until he was bent over the edge of it at the end. Phil tied his hands together behind his back and put the spreader bar back on his knees and ankles. Dan felt Phil mess with the dildo inside of him, and when he was done, he found it seemed to be held in place by something. He almost asked what it was, until he suddenly found the toy slamming in and out of him faster and harder than he thought possible. He cried out in surprise as he was suddenly being fucked mercilessly with the toy, eyes filling with tears again.  
He struggled against his restraints, practically sobbing with pain. He felt Phil's hand connect sharply with his bum, and he cried out again. "Stop struggling, you little bitch," Phil growled, grabbing Dan's hair and tugging it roughtly. "You brought this onto yourself, now take it like a good little whore."  
"I'm sorry!" Dan practically shouted, knowing he was speaking out of turn but unable to stop himself. "I'm sorry, I'm sorry, I'm sorry! Please, it hurts! It hurts!" He was red in the face from how hard he was sobbing, his face covered with salty tears. "I'll do anything! Please! Please, I'll do anything! Just make it stop!" He was begging and sobbing, truly willing to do anything at that moment. He sniffled a bit when he felt the toy slowing down a bit. He turned his head slightly and saw it was attached to a machine that was moving it back and forth, and the machine was slowing down.  
"Anything, huh?" Phil asked, a smirk on his face. Dan sniffled again and nodded quickly, trying to pull away from the toy but unable to do so. "Alright then. If you're so sure about it, I'll take you up on that offer." Dan didn't like the sound of that. But it was too late, as Phil had already turned the machine off and slid the toy out of him, and was in the process of unrestraining Dan. As soon as he did, he got a washcloth like the one he had before, a wet one, and began cleaning Dan out, soothing the inflamed ring of muscle.  
Once that was done, Phil once again cleaned off Dan's face, then helped him back onto the bed in a laying position. Dan was surprised when Phil covered him with the blanket, tucking him in. "Get some rest, toy. I'll make sure you keep up your end of the deal, once you're rested enough to stay awake for it." Dan wanted to protest, but the bed was so comfortable, the sheets so soft and the duvet so warm. And as soon as Phil picked up the remote controlling the electronics in the room and used it to turn the lights down, Dan's exhaustion finally overtook him, and he fell asleep.

**Notes for the Chapter:**

> Like I said, I DO NOT CONDONE THESE ACTIONS. This isn't supposed to be a romance story. Phil is not treating Dan correctly. If you are in a situation like this in your real life, contact a close friend or the police or someone you trust, and get help immediately.


	3. Part 3 - Locked Away

**Summary for the Chapter:**

> Dan finally wakes up, and decides to disobey his master's orders. This can never end well.

**Notes for the Chapter:**

> As always, I DO NOT CONDONE THESE ACTIONS. THIS IS NOT A LOVE STORY. DO NOT READ IT AS IF IT WERE ONE.

When Dan finally awoke and slowly opened his eyes, he could easily tell by looking out the window that at least a good bit of time had passed. It had been nearing sunset when he dozed off, and it was pitch black out now. Then again, he had been through so many exhausting things for his punishment. Speaking of...

Dan felt his stomach drop when he remembered how he agreed to do anything to get out of his punishment, and the look Phil had given him when they made the deal. Dan sighed softly, deeply regretting his choice. He had just been in so much pain, he just wanted it to be over.

Dan sighed softly and sat up slowly to stretch, wincing when he felt how sore his muscles were. He couldn't tell if it was from the abu- no, punishment, he had been through earlier. Or maybe it was from how long he'd been laying in one position. He supposed it would depend on how long he was there. It certainly couldn't have been more than a few hours...

Dan was forced out of his thoughts when the door to the en suite bathroom opened, and out stepped his owner Phil, who looked surprised to see Dan sitting up. Dan noticed he was dressed differently than normal, looking more appropriate for a club rather than an event where his usual suit and tie would be required.

"Oh, good. You're awake," Phil said with a smile, walking over to the bed and sitting next to Dan. "You're going to get up and go take a shower, and when you get out, there will be specific clothes waiting on the bed for you. You are to put them on and then come meet me in the lounge. Understood?"

"Y-yes, sir. It understands," Dan spoke softly, his head down to show submissiveness. "I-it will do as it is told." He needed to be on his best behavior. He didn't want to risk being punished again.

"Good. Just like it should." Phil's smile became a bit darker, his eyes narrowing. "Because if it doesn't, it will get a severe punishment instead of a moderate punishment." Dan tensed up at that. If this was a moderate punishment, he didn't even want to imagine what a severe punishment would be. Phil stood up, straightening his shirt before walking to the door and leaving, shutting the door behind him to leave Dan alone to get ready.

Dan sighed softly and stood up, shivering as he was no longer under the blankets. He slowly stepped towards the door to the bathroom, stepping in and shutting the door behind him. He looked at the familiarly luxurious bathroom then walked over to the large shower, adjusting the settings according to how he preferred it. He turned on all of the faucets to hot water, both the overhead main one, as well as all the ones at the walls, a small groan slipping out as the heated water hit him from all angles, instantly relaxing his sore muscles.

Dan simply stood there for a few minutes, hit eyes closed as he tried to relax, but he knew that soon he would have to work on properly getting clean. He eventually went through the motions of cleaning his hair and body, the constant stream of hot water making him feel so much better. He wanted to just stay in the shower forever.

But sadly, that was not an option.

Once he was cleaned off and had no more soap on him, he oh-so reluctantly turned off the shower. He stepped out and picked up the towel hung out on the heating rack, quickly wrapping himself in it and beginning to dry off. He dried his body off then wrapped the towel around his torso, stepping over the sink once he was covered. He was so thankful these floors were heated, because he was sure that if they weren't, he'd be shivering right then.

Dan went about getting ready in the bathroom, putting on his deodorant, brushing his teeth, drying and straightening his hair, and putting healing cream on the still healing cuts along his side, from when Phil had gotten particularly rough the previous week. Dan certainly wasn't complaining about that one, though. Certainly not when it had felt so great.

That was the thing, wasn't it? That's why Dan so willingly stayed. Because while he hated the rules and punishments, he still loved the times where Phil made it feel good. All he had to do was follow Phil's rules, and then he would get the nights of his life, every single night.

Dan looked down and noticed a noticeable bump in the front of his towel, blushing as he realized that just thinking about Phil doing such things to him got him hard. He quickly reached down to readjust himself, trying to hide it. If Phil's attired earlier was anything to go by, they were going to be going out. And he really, really didn't want other people to see him getting hard.

He had no idea what was in store for him that night.

He stepped out of the bathroom and back into the bedroom, the towel still around his waist. He walked over to look at the clothes on the bed, finding a few odd things. The first thing he noticed was the egg vibrator with a string on it and lube sitting next to it. The second thing he noticed was the note card next to them, telling him that he was to put the vibrator inside himself before putting his clothes on. And the last thing he noticed was how little clothing was actually there.

There were a pair of black panties that looked like they would barely even keep his cock inside of it, as well as a jean skirt that looked more like a belt than actual clothing. Then there was a thin white crop top with sleeves that would barely cover his shoulders, and was obviously made for people with plenty of cleavage to show off. Then, sitting next to his normal clothes was a pair of black platform heels that looked impossible to walk in, as well as a pair of dangly black earrings and matching necklace and bracelet.

Dan sighed and removed the towel, dropping it in the hamper before starting to pull his clothes on. He had no other options. If he tried to avoid wearing the clothes, he would get into so much more trouble. It wasn't worth it. His dignity wasn't worth the risk of pain. And besides, he wasn't exactly opposed to wearing a skirt. His biggest problem was how thin the shirt was and how short the skirt was. Really, he would be fine otherwise. He had always been a firm believer that clothes don't have gender, and this was no exception.

Dan finished putting the clothes and jewelery on and slowly walked over to the full-length mirror on the wall, his steps shaky as he adjusted to walking in the heels. He looked at his reflection, blushing when he realized he actually liked how he looked. Sure, it showed a lot more than it covered, but damn if it didn't make him look good. And the skirt sat perfectly to show off the curve of his arse perfectly so that it hardly looked flat like he felt it normally did.

After looking at his reflection and admiring how he looked, he slowly walked to the door and stepped out, occasionally having to hold onto the wall for support. He walked slowly to the lounge, still struggling but slowly getting the hang of it. He stepped into the moderately sized sitting area, surprised to find that it wasn't just Phil sitting there, but also a woman with multiple make-up cases sitting on the floor by her feet. Oh no.

Phil turned and saw Dan standing there, smiling and standing up. "There you are. I was wondering how long it would take. We wouldn't want to be late, would we?" Phil walked over and took Dan's hand, leading him further into the room and sitting him down in a chair across from the woman. "Dan, this is Caroline. She's going to be doing your make up before we go. Caroline, this is Dan, who I've told you so much about."

Caroline gave him what was clearly a forced smile. She began opening her make up cases, and her silence made Dan more nervous. Until she looked at Phil and lifted her hands, moving them and gesturing in ways that was so obviously sign language.

Dan watched in awe as Phil lifted his hands, clearly signing back. Dan couldn't tell what was being said, but it was clear Caroline was upset about something. Eventually, Phil glared at her and signed something, resulting in her huffing and finally taking her make up out, gently taking Dan's face and starting to apply make up.

Once their apparent discussion was over, Phil sat down near them, keeping his eyes locked on Caroline, most likely to make sure she did Dan's make up the correct way. Dan tried to keep as still as possible while she applied many creams, powders, and other substances that Dan couldn't name for the life of him.

By the time Caroline finally finished, Dan's left foot had long since fallen asleep, and he was sure he had a cramp where he was sitting. Caroline pulled back and began putting her make up away, then took out a small mirror to show him. Dan gasped when he saw his own reflection. She had contoured his cheeks perfectly, so perfectly that it looked completely natural. His lips were a slightly dark purple on the inside, lined by a dark red. They were the perfect shade that it was hard to even tell he had two colors on. His eye lashes looked longer and thicker, and the winged eyeliner went perfectly with the glittery, dark eyeshadow that was so lightly applied that it seemed barely there. Any signs of blemishes were gone, covered by whatever products she had used, and he was practically glowing with beauty.

Caroline and Phil both looked at him, seeming to be awaiting his reaction. "I-I love it..." He murmured, slightly afraid to speak, as if that would make it all disappear. He noticed that Caroline seemed ecstatic with his response, while Phil simply nodded, not seeming to truly care about how he felt about the make up. Caroline went back to putting her make up away, seeming to be much happier than before.

Caroline and Phil signed to each other for a bit before Caroline finally stood up, giving Dan a smile and waving goodbye before walking out, and Phil quickly took his spot to sit across from Dan.

"So how does it feel about the heels?" Phil asked Dan, who shrugged slightly.

"I-it can barely walk in them," He admitted. Phil nodded and smirked.

"Perfect." Phil leaned down and fiddled with the shoes a bit, making sure the straps were tight enough that Dan wouldn't fall out of it. Then he suddenly pulled a pair of small locks out and put them on the shoes, causing Dan to gasp as he realized he had no way of getting out of the shoes.

"I-is it not allowed to take the shoes off?" Dan asked quietly. Phil chuckled and shook his head.

"No. Because I love knowing that it can't even really try to run away." Dan blushed bright red as Phil stood up, taking his hand and helping him up as well. "Now, go into the kitchen and get me the pink remote sitting on the counter. It'll be the same shade as the little toy that had better be inside of you right now."

Dan blushed but nodded. He quickly went into the kitchen, then froze as he realized what this meant. If he brought this remote to Phil, he knew it would be used against him. But what other choice did he have? Maybe if he just...

Dan quickly grabbed it and put it into his back pocket, then walked back to where Phil was, his head bowed. "It couldn't find the remote, sir. It is very sorry, but the remote doesn't seem to be on the counters."

Phil raised an eyebrow, looking mildly annoyed. "Oh, really?" He asked, and Dan nodded. "Turn around. Now." Dan hesitated before turning around, tensing up as he felt Phil slide the remote from the pocket of the jean skirt. "Well it seems that my toy lied to me, and hid the remote from me. Does it know what that means?" Dan shook his head know. He wasn't sure he wanted to know what it meant. "It means that it's in even more trouble now than before."

Phil grabbed Dan's hair roughly and pulled hard, causing Dan to let out a yelp as he lost his footing, falling flat on his bum. He cried out in pain as he was dragged across the floor by his hair, then down the stairs to the basement. He was nearly sobbing by the time they got there, and his make up was completely messed up by then.

Phil tossed him roughly onto the floor, then shut the door loudly behind them. He turned on the hanging light above them, and Dan whimpered at how angry he looked. Phil suddenly took out his phone, tapping a few things and then pointing the camera part of it at a terrified Dan.

"Say hello to everyone, Dan. Go on, say hi." Dan hesitated but then raised his hand, waving at the camera. "Good. Now, why don't you tell everyone what you did."

Dan blushed and looked down, his hands shaking. "I-I lied, a-and didn't listen to what you told me to do." Phil nodded and gestured at Dan to continue. "A-and I h-hid the remote to the toy from you."

"That's right. And you were already being punished, weren't you?" Dan nodded, fidgeting a bit. "And while that isn't quite worthy of a severe punishment, it's certainly worthy of making your punishment worse." Phil held the remote and turned the dial then pressed a button, causing Dan to moan as the egg inside of him started vibrating. "Oh, but that's something that feels good, isn't it? Not much of a punishment." Phil used his foot to push Dan so he was laying on his back, then to move the skirt up to almost completely expose Dan's lower bits to the camera.

Dan fidgeted, trying not to show that it felt good. He didn't want to be punished. But it didn't work. Phil went about setting the phone up so Dan could be seen on it, but Phil didn't have to hold it. Then, Phil dragged the aroused boy towards the wall, quickly putting a metal collar on him, then attaching it to the wall with chains. Then Phil handcuffed Dan's hands to the collar, right at his neck, so hit arms and hands were nearly useless.

Phil set up the phone so it was plugged in and therefore wouldn't run out of battery power any time soon, meaning it could record for quite a while. Phil walked up to Dan, who was leaning against the wall that his chain was attached to. He grabbed Dan's chin roughly, forcing him to look at Phil.

"I'm leaving you here for now. When I come back, I'll have a better camera. Then I'll leave you here alone again, and when I come back from that, I promise I won't be alone. This part of your punishment is just so you're completely sensitive when the next part starts." Phil smirked evilly. "Darling, this is only the beginning. And I suggest you get used to dry orgasms, because eventually that's what you're going to get. And I'm still not turning it off then."

Dan whimpered, preparing to say something, but then Phil took a piece of duct tape and put it over his mouth, rendering him nearly silent. Dan whined as he watched Phil move the panties and the skirt so he was competely exposed to the camera, then walk back to the door and leave, locking it behind him.

Dan hated how aroused this sort of treatement made him.

**Notes for the Chapter:**

> Wow that was longer than I expected. I'm sad to say I have to split it into two chapters, originally the next chapter was gonna all be in this chapter(and this chapter and that chapter were gonna be chapter two) but it ended up being much too long.  
> And next up: gangbang! (my personal fave kink tbqh)


End file.
